Unique Phenanthrenes from

Juncaceae Juncus ensifolius antiproliferative combination assay doxorubicin phenanthrene synergism

Journal

Pharmaceutics
ISSN: 1999-4923
Titre abrégé: Pharmaceutics
Pays: Switzerland
ID NLM: 101534003

Informations de publication

Date de publication:
10 Mar 2022
Historique:
received: 11 02 2022
revised: 07 03 2022
accepted: 08 03 2022
entrez: 26 3 2022
pubmed: 27 3 2022
medline: 27 3 2022
Statut: epublish

Résumé

Phenanthrenes are the main special metabolites of Juncaceae species from phytochemical, pharmacological, and chemotaxonomical points of view. The present study focused on the isolation, structure determination, and pharmacological investigation of phenanthrenes from Juncus ensifolius. Nineteen compounds, including 17 phenanthrenes, were identified from the methanol extract of the plant. Thirteen compounds, namely, ensifolins A−M (1−13), were obtained for the first time from natural sources. Four phenanthrenes [2-hydroxy-1,7-dimethyl-5-vinyl-9,10-dihydrophenanthrene (14), juncuenin B (15), juncatrin B (16), and sylvaticin A (17)], 4-hydroxybenzaldehyde (18) and luteolin (19) were isolated for the first time from J. ensifolius. Ensifolins A (1) and B (2) are structurally unique phenanthrenes, considering that they are flavonoid- (1) or benzaldehyde-adducts (2). The antiproliferative activity of all isolated compounds against HeLa, COLO 205, and COLO 320 cancer cells and a non-tumor (MRC-5) cell line was tested using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) viability assay. The luteolin-substituted phenanthrene ensifolin A (1) proved to be the most active against all three cancer cell lines (IC50 values 3.9−12.7 μM) and showed good selectivity (SI = 4.95) in the case of COLO 205. The best selectivity was recorded for ensifolins D (4, SI > 5.15, HeLa), H (8, SI > 8.13, HeLa), and 17 (SI > 9.43, HeLa). The synergistic activity of the compounds with doxorubicin was also tested on HeLa cells, and ensifolins E (5) and H (8) exhibited very strong synergism (CI < 0.1). In conclusion, these phenanthrenes are worthy of further investigation.

Identifiants

pubmed: 35335985
pii: pharmaceutics14030608
doi: 10.3390/pharmaceutics14030608
pmc: PMC8949129
pii:
doi:

Types de publication

Journal Article

Langues

eng

Subventions

Organisme : Ministry of Human Capacities
ID : GINOP-2.3.2-15-2016-00012
Organisme : Ministry of Human Capacities
ID : UNKP-20-3-II
Organisme : Ministry of Human Capacities
ID : EFOP-3.6.3-VEKOP-16-2017-00009
Organisme : National Research, Development and Innovation Office
ID : K128963

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Auteurs

Dóra Stefkó (D)

Department of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, 6720 Szeged, Hungary.

Norbert Kúsz (N)

Department of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, 6720 Szeged, Hungary.

Nikoletta Szemerédi (N)

Department of Medical Microbiology, Albert Szent-Györgyi Health Center, Albert Szent-Györgyi Medical School, University of Szeged, 6725 Szeged, Hungary.

Anita Barta (A)

Department of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, 6720 Szeged, Hungary.

Gabriella Spengler (G)

Department of Medical Microbiology, Albert Szent-Györgyi Health Center, Albert Szent-Györgyi Medical School, University of Szeged, 6725 Szeged, Hungary.

Róbert Berkecz (R)

Institute of Pharmaceutical Analysis, University of Szeged, 6720 Szeged, Hungary.

Judit Hohmann (J)

Department of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, 6720 Szeged, Hungary.
Interdisciplinary Centre of Natural Products, University of Szeged, 6720 Szeged, Hungary.

Andrea Vasas (A)

Department of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, 6720 Szeged, Hungary.

Classifications MeSH